Permanent Virgin Pegging Stories

58,250 results
Orientation
Length
Source
Infinite Scroll

Made to Obey Ch. 07

by madetoobey on Jul 10, 2019
Transgender & Crossdressers

Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...

My First Pegging Experience

by doncamillo on Nov 19, 2018
Fetish

When I mentioned my interest in pegging to my professional dom friend her eyes sparkled. We were out drinking and have had quite a lot of drinks already. So it wasn't surprising that we ended up in her studio to satisfy my curiosity. After we got in she put her bag to the side, took off her jacket, helped me take mine off and stood in front of me. Looked u...

A late night at the office

by morpheus_arms on Aug 30, 2019
Miscellaneous

This is a Hub Page to make it easier to select a path the reader would enjoy most right from the start and as such very much a WIP. {Morpheus here: This story is what Germans call a "Fingerübung", a finger excercise to test out how to structure and maintain a first complex story all of my own. As such, expect some newbie mistakes and such, even tho...

Open in Reader

Laura's Femdom Empowerment Ch. 04

by Long2bLocked on Jan 15, 2019
BDSM

Chapter 4 Going Pro It was late January and I decided it was time for some new excitement. I had broken up with Jared a few months prior and I wanted a new sub guy to torment. I was thinking about the best place to find a submissive guy and suddenly I remembered Leesa looking for costumes the previous Halloween. She wanted me to go to the party as a domin...

It's not All About Her

by Copycat88 on Sep 17, 2017
Fetish

DISCLAIMER: This story is about Femdom, Cross Dressing and Cuckoldry. If these topics offend you please don't read it... Just move on. No need to vote or comment if this isn't your "thing". If these appeal to you, please enjoy. ***** -IT'S NOT ALL ABOUT HER- I absolutely hate trying to get anything off of my husband's computer, but here I was trying and...

Busting at Work, Induction

by JJA122 on Sep 21, 2020
BDSM

Notice: Readers and characters are 18+ This is fiction. And a BDSM story, Emphasis on the S. It includes fetishes such as Femdom, CBT, CFNM, humiliation, chastity, pegging. It is a ballbusting story foremost, where our guy gets hit in the testicles. If that doesn't sound like your thing, you WILL NOT READ OF IT. This story continues and concludes events fro...

Cul-De-Sac: A Story in Around Ch. 03

by ZotDragon on Sep 13, 2017
Novels and Novellas

"Put down those damn binoculars!" Gina raged at Roger. He had been at the tinted window for most of the evening. "He had two women over tonight, the new girlfriend and the regular slampiece," Roger reported eagerly while reluctantly putting the high-powered binoculars onto the shelf next to the window where he did his regular viewing. "You're going to get...

Creampies, Pegging & Intimacy

by Here4u2get on Nov 18, 2019
Erotic Couplings

I had to laugh when I heard the music playing and the shower running behind the door of the master bathroom. Dana, my wife, apparently had the same plan as I did about getting ready early that Saturday evening before we met her girlfriend and husband for dinner. Yes, she wanted to see as much of the football game as she could before we had to leave. Though...

Sissified by My Sister

by GreenGale on Sep 11, 2017
Transsexuals & Crossdressers

I will never forget that night. The night I discovered how I truly am. My true self. Its an unforgivable night. And I never thought my little sister would be the one to help uncover this part of me. I was a young, average 19 year old, my sister and I were home from college for winter break. I had short, blond hair and my sister had brown hair cut about at h...

Getting Pegged

by pegboy on Jul 15, 2020
Toys & Masturbation

Hank always thought his sister's significant other Lisa was sexy. Even though she had an air 'butchness' about her. Lisa's hair was done up feminine. She wore dresses occasionally to work and she used makeup. But she had a mannish way of walking and talking. She relished dirty jokes and just like men she made the occasional inappropriate sexual remark. She c...